Kyra Maya Phillips: on literature, compassion and deviant creativity

The co-author of 2015 bestseller The Misfit Economy shares the creative inspiration she found in the stories of pirates, gangsters, bootleggers and hackers.

Emily Yates
Sep 28, 2017 · 7 min read

Over the past decade, there has been a growing taste in publishing for “unconventional innovation”, as the tech and business markets have tracked the dream of disruption to the fringes of society itself. The Misfit Economy (2015) is one of the most adventurous books so far — with co-authors Alexa Clay and Kyra Maya Phillips taking on 30 case studies for their analysis; including Somali pirates, Chinese bootleggers, computer hackers, street gangs and political activists. From these stories, the authors proposed five key principles towards a theory of the ‘deviant’ creative method; hustling, copying, hacking, provoking and pivoting.

A project four years in the making, The Misfit Economy took both women around the world and Kyra Maya Phillips, a former journalist, deeply into her passion for biographical writing — identifying the neglected stories capable of breaking down mythologies around creativity:

“We were both pretty dismayed about all the books that were coming out about creativity and how everything focused on people that everybody knows and feels comfortable with — people like Steve Jobs and Henry Ford, and companies like Google and Apple. That’s not to say they’re not creative and you can’t learn a lot from them — we just felt like there was another message that needed to be part of that conversation. It started off as the informal market and then we widened it to all of the informal and black market economy.”

In opening up the illicit economy, Kyra is aware of the dangers of replacing one mythology for another, and says she is wary of the misfit becoming “another overused trope”. For her, each story is unique, and intended to promote compassion in the reader:

“I hear from people who loved the book for its irreverent message and compassion, and that’s what I loved about it too. It was an interesting experience for me — whenever I was interviewed and challenged whether I felt compassion for someone who had committed a crime — it was interesting for me to say that I did. That was a very significant change for me. I can’t predict or say with certainty what impact the book had — but my hope is that it softened people a little bit and developed their ability to think less black and white about others. There’s always a level of compassion that I think you’ve got to work hard to reach but it’s always there, and my hope for the book was always that.”

The story that impacted Kyra the most was that of Duane Jackson, who has since become a feature of her excellent talks on the subject. After a turbulent upbringing in children’s homes all over east London, Duane was on the verge of being institutionalised when he was told by a child psychologist he would grow up to be “either a master criminal or an extremely successful business man.” His circumstances led him first to attempt the former; until his criminal career ended abruptly at the age of 20, when caught in the act of smuggling 6,500 ecstasy pills to the USA. A decade later, he arrived at the latter — selling his accounting software platform Kashflow for an amount rumoured to be in the tens of millions.

The two and a half years Duane spent in prison were transformative, and full of the ‘hacks’ that Kyra and Alexa describe as part of the deviant methodology. These might include: cooking beans on toast with a plastic bottle and a prison mattress; writing code by hand in prison and fixing bugs over the phone while incarcerated; or indeed the stroke of genius that was eventually the key to his success. As an online programmer without the coding skills for desktop, Duane built his accounting software online — inadvertently creating one of the first cloud-based subscription models back in 2005.

On the surface level the stories are those of misfits struggling against their limitations. But Duane’s goes further — it was not the struggle that changed him but the effects of prison, where he had an awakening moment about what his life had become. With nothing to do but think, he was able to switch off the auto-pilot and consciously decide to live with intention — a moment of dramatic personal change which, in terms of the book’s methodology would be described as ‘pivoting’. This, combined with his instinctive persistence and hustle, was the key to Duane’s success, and the reason that Kyra connected with him so strongly.

Of the five tactics of deviant innovation depicted in the book, I asked Kyra which resonated with her most.

“‘Provoke’ to me was very interesting. To provoke means to spark dialogue, and could mean so many things to so many different people. To me, it meant the ability to imagine an alternative reality. Not just any alternative reality — an alternative reality that you can marry to the present moment. If you want to make real tangible and physical change, like change a policy or start a business that will change consumer behaviour, then that alternative reality needs to translate into where we are. I was very shocked and surprised at the ability of thinking that way to really get things going on the ground. People who work at NASA often point to a story by Jules Verne in which the first time that a man went into space was mentioned. That to me was interesting; the power to put yourself in an alternative universe even for a brief moment and how that can get your mind on a different road to come up with better ideas or think more creatively.”

Over a wide-ranging conversation with Kyra about criminality, compassion, Buddhism and, most of all, literature, it was clear that these fundamental ‘leaps of perspective’ interest her the most. If these are the moments of creative inspiration that decide the direction of one’s life — what realisation, or ‘pivot’, has done the same for her?

“I grew up with the view that everything is personal, that things happen because you are you — and that is a very, very hard way to live. It gives a narrative to events that makes already painful things even worse. I read this book by Joan Didion — The Year of Magical Thinking — about the year she experienced after her husband of 30 years passed away very suddenly. She talks about having a geological perspective on the world. She believes that we are like the world in that a hurricane or an earthquake is not personal — it just happens. Something really clicked for me in that moment. This, in combination with reading a lot about mindfulness and practising meditation. Literary fiction has an ability to get you inside someone’s head and has an impact in destroying the thought that it’s all about you — everybody is in some sort of suffering. So, i think reading is really, truly important. I love that feeling of hearing myself in someone else. It’s so affirming, it’s really, really wonderful. That’s the biggest change in my life i would say — discovering books — there’s nothing that has affected my life more.”

Kyra’s greatest literary influence is Michel de Montaigne, the 16th century French essayist she calls the “godfather of blogging”. Like Kyra, de Montaigne was obsessed with studying cultures wildly different to his own, always reflecting on how absurd his own behaviour might appear to those from an alien culture. It’s exactly the quality that Kyra attributes to the misfits in her book — that they too have an incredible ability to question both the world around them and, most importantly, their own behaviour.

“Michel de Montaigne just got it. He got how to be human, you know. If you read his essays, you will see that he really understood how to live. He was very mindful which is really interesting to me… you go back to the 1500s and there’s this guy who has never heard of the mindfulness stuff — he just knows. I love his obsession with relativity, that one thing might be acceptable somewhere but unacceptable somewhere else; that really is deep compassion and I’m attracted to that. There’s a story about a cat that I love — “When I’m playing with my cat, how do I know she is not playing with me?” So, there is this other person here — even a cat! — it’s got a whole entire existence and yet we are so focused on ourselves, our sense of self and the idea that the world revolves around us! He didn’t judge himself harshly, which I really liked as well — you know, he said people change all throughout their lives. And just like if you had a dinner party and you wouldn’t judge everyone who walked through the door, just take that attitude towards yourself and all your past selves.”

Kyra makes the point that we don’t have to wait to be thrown into prison or dragged into desperate circumstances to choose how we derive meaning from experience. What’s more important is to take a step back and observe the cultures of others, as well as our own entrenched habits, thoughts and behaviour. The compassionate experience of literature is just one shortcut on the route to experimental thought.

It may not surprise you to learn that literature is where Kyra sees her future. Now settled in Australia with a young family, she calls herself a ‘bookseller, reader and writer’ and is considering taking an MA in Creative Writing when her new baby is a little older. In the meantime, she’ll pay us a visit in Brighton this November to share the depth of her experiencing acting as a biographer to the worldwide deviant economy.

You can hear more about The Misfit Economy at the Meaning conference in Brighton, UK on 16 November 2017 — where Kyra Maya Phillips will join a line-up of diverse speakers exploring the role of business in creating a more sustainable, equitable and humane world. Find out more via the event website.


Meaning connects and inspires the people who believe in…

Emily Yates

Written by

Writer, researcher and strategist working in arts, tech and public transport. Co-founder of @ABCommuters



Meaning connects and inspires the people who believe in better business | 14 November 2019 — Brighton UK

More From Medium

Also tagged Pirates

Also tagged Pirates

The Gentleman Pirate

Also tagged Emotional Intelligence

Top on Medium

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade